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POLYMER SCIENCE    

https://doi.org/10.1007/s10118-020-2450-6 Chinese J. Polym. Sci.

Syntheses of Soluble Biopolyimides Using 4-Aminophenylalanine Kenji Takadaa, Hiromasa Shinagawaa, Yuki Moritaa, Manjit S. Grewala, Kazuya Tayaa, Amit Kumara,b, and Tatsuo Kanekoa* a Graduate

School of Advanced Science and Technology, Energy and Environment Area, Japan Advanced Institute of Science and Technology (JAIST), 1-1 Asahidai, Nomi, Ishikawa, 923-1292, Japan b Material/Organometallics Laboratory, Department of Chemistry, Atma Ram Sanatan Dharma College, University of Delhi, New Delhi- 110021, India

 Electronic Supplementary Information Abstract   4-Aminophenylalanine (4APhe), an exotic amino acid which is obtained as a microorganism metabolite of glucose, is polycondensed with various tetracarboxylic dianhydrides as a diamine monomer to obtain poly(amic acid)s. Subsequent thermal imidization of poly(amic acid)s is made at 220 °C with stepwise heating from 100 °C. Some of the obtained polyimides (PIs) exhibited good solubility in organic solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, and more. The progress of imidization was observed by proton nuclear magnetic resonance and infrared spectroscopy to confirm that the imidization ratio was up to 98%. Carboxylate group of the side-chains of PIs affected their solubilities despite the high imidization ratio, and the solubility was lost for any organic solvents by decarboxylation at 280 °C, confirmed from mass-loss of thermogravimetric analysis. Thus, a new series of PIs were obtained with abilities of solvent-molding in PI state and thermal resistivity enhancement by further heating after molding. Keywords   Bio-based polymers; Polyimides; Amino acids; 4-Aminophenylalanine; Soluble polyimides Citation: Takada, K.; Shinagawa, H.; Morita, Y.; Grewal, M. S.; Taya, K.; Kumar, A.; Kaneko, T. Syntheses of soluble biopolyimides using 4aminophenylalanine. Chinese J. Polym. Sci. https://doi.org/10.1007/s10118-020-2450-6

 

INTRODUCTION In order to build a sustainable society, the development of biobased polymers, which are materials obtained from plants that fix atmospheric carbon dioxide in their body, is urgently required.[1] Due to those enormous achievements, various biobased polymers have been developed in the world.[2−4] Poly(lactic acid)s are the representative bio-based polymers, and give various functions to expand the range of applications.[5,6] However, there are only a small number of reports on the high-thermoresistance bio-based polymers because almost conventional bio-based polymers contained ester bonds in polymer backbones. Furthermore, if a biocompound such as an amino acid obtained by fermentation can be used as a starting material for polymers having high thermal stabilities and durability, materials development independent of petroleum industry can be performed. In addition, such durable bioderived materials can be expected to fix carbon dioxide from the atmosphere and store inside them for a long time. The highly heat-resistant bio-base